1. Field of the Invention
The present invention relates to a novel radical-polymerizable silicone and a production process for the same, specifically to polymerizable terminal group-containing polyorganosiloxane having a polyoxyalkylene segment between a polymerizable terminal group and a polysiloxane segment and a production process for the same.
2. Description of the Related Art
Subjecting cyclotrisiloxane to ring-opening polymerization with an organic lithium compound or lithium silanolate used as a polymerization initiator and then terminating the reaction with an end-capture having a radical-polymerizable functional group has so far produced a radical-polymerizable silicone. A production process disclosed in Japanese Patent Application Laid-Open No. 78236/1984 in which hexamethylcyclotrisiloxane is subjected to ring-opening polymerization with lithium trimethylsilanolate used as a polymerization initiator and then sealed with 3-(2-methacryloyloxyethoxy)propyldimethylchlorosilane can be given as an example of a production process for dialkylpolysiloxane having an acryl or methacryl group at a single terminal. Further, a production process disclosed in Japanese Patent Application Laid-Open No. 110303/1985 in which hexamethylcyclotrisiloxane is subjected to ring-opening polymerization with lithium trimethylsilanolate used as a polymerization initiator and then sealed with p-vinylphenyldimethylchlorosilane can be given as a production example for dialkylpolysiloxane having a styryl group at a single terminal.
The radical-polymerizable silicone described above can produce graft polymers by copolymerizing with various monomers. These graft polymers are used for high molecular products such as various films, plastics, rubber and waxes, surface treating agents for glass and paper and, modifiers for shampoos, rinses and hair setting agents. Thus, these products are provided with functions such as water repellency, a stain resistance, a non-adhesive property, a heat resistance, an abrasion resistance and a biocompatibility. These graft polymers have dialkylpolysiloxane bonds on side chains and do not have such problem that dialkylpolysiloxane bleeds out unlike conventional compounds obtained by merely blending dialkylpolysiloxanes.
Applications of such graft polymers having radical-polymerizable silicone include hair care products, skin care products, make-up cosmetics, water-in-oil type emulsion cosmetics, oil-in-water type emulsion cosmetics, contact lenses, glazing agents for floor, synthetic leathers, coating agents for an optical magnetic storage, magnetic paints, adhesives, water repellent finishing paints, aqueous resin emulsions, surface modifiers for a high molecular material, resin compositions for electrodeposition paint, subaqueous stain preventives for ship bottom paint and water-repellent and oil-repellent agents.
However, conventional polymerizable terminal group-containing silicones have an ester bond between a radical-polymerizable group and a polysiloxane segment and therefore are susceptible to hydrolysis, so that it is difficult to use them for a long period of time in moist atmosphere.
On the other hand, in order to solve such problem, amide bond (not ester bond) type single radical-polymerizable terminal group-containing silicones are disclosed in Japanese Patent Application Laid-Open No. 017577/1993.
However, conventional single radical-polymerizable terminal group-containing silicones including amide bond type single radical-polymerizable terminal group-containing silicones described above do not fall in a homogeneously mixed state in a certain case, and therefore it has been difficult to graft silicone depending on monomers to be copolymerized. Further, when carrying out emulsion polymerization, it has been difficult since silicone has an inferior dispersibility into water.